TW201427967A - Bipolar compound having quinoline and carbazole and organic light emitting diode device using the same - Google Patents

Abstract

The present invention is related to a bipolar compound having quinoline and carbazole. The compound has a structure of formula (I) as follows: wherein A is phenyl, biphenyl or terphenyl; Ra, Rb and Rc are independently selected from a group consisting of H, halo, cyano, trifluoromethyl, amino, C1-C8 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C3-C20 cycloalkyl, C3-C20 cycloalkenyl, C1-C20 heterocyclic alkyl, C1-C20 heterocyclic alkenyl, aryl and heteroaryl. A host material, a dopant and an organic light emitting diode device including the above-mentioned compound are also provided herein.

Description

Bipolar compound containing quinoline and carbazole and organic light emitting diode thereof

The present invention relates to a novel bipolar compound, and a host luminescent material and organic light emitting diode device comprising the same. More specifically, the bipolar compound is a bipolar compound containing quinoline and carbazole.

Organic electroluminescence is an spontaneous electroluminescence (OEL), which refers to the phenomenon of luminescence of organic substances excited by corresponding electric energy under a certain electric field. In recent years, the research on organic electroluminescence has made a breakthrough development, which has caused a boom in domestic venture capital and optoelectronic industry investment. Organic electroluminescence The principle of light is similar to that of inorganic materials, and is generally classified into two types: small molecule organic light-emitting diodes and macromolecular organic light-emitting diodes, in which small molecule organic light-emitting diodes are small molecule dyes or pigments. It is the main body of the component material, and the macromolecular organic light-emitting diode is mainly composed of a conjugated polymer organic material.

The key to determining the goodness of organic light-emitting diode products lies in materials. The light-emitting materials are the most important materials. Good light-emitting materials must meet four conditions: (1) high quantum efficiency, fluorescent characteristics, and fluorescent spectrum. Distributed in the visible light region of 400~700 nm; (2) good semiconductor characteristics, high conductivity, ability to conduct electrons or holes, or both; (3) good film formation, in tens of No pinholes are formed in the film of rice; (4) Good thermal stability.

The development of luminescent materials is a very important topic, especially the main body. The luminescent material, the main luminescent material must have easy to capture carriers, good energy transfer characteristics, high glass transition temperature, high thermal stability, suitable singlet and triplet energy gaps. Furthermore, in addition to luminous efficiency, the component life of the luminescent material is another requirement. Therefore, the organic light-emitting diode still has a lot of room for improvement in the development of the host light-emitting material.

The present invention provides a bipolar compound containing quinoline and carbazole having the structure shown in the following formula (I): Wherein A is phenyl, biphenyl or triphenyl; R _a , R _b , R _c are independently selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, amine, C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, C ₂ -C ₁₀ alkynyl, C ₃ -C ₂₀ cycloalkyl, C ₃ -C ₂₀ cycloalkenyl, C ₁ -C ₂₀ heterocycloalkyl, C ₁ -C ₂₀ heterocycloalkenyl a group consisting of a aryl group, an aryl group, and a heteroaryl group.

In one embodiment, A may further have a substituent consisting of hydrogen, halogen, cyano, trifluoromethyl, amine, C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ olefin , C ₂ -C ₁₀ alkynyl, C ₃ -C ₂₀ cycloalkyl, C ₃ -C ₂₀ cycloalkenyl, C ₁ -C ₂₀ heterocycloalkyl, C ₁ -C ₂₀ heterocycloalkenyl, aryl And heteroaryl.

In one embodiment, the aforementioned aryl group may be a phenyl group or a substituted benzene group. base. Here, the substituted phenyl means a halogen, an alkyl group, an alkylbenzene or a heteroaryl group, but is not limited thereto.

In one embodiment, the aforementioned heteroaryl group may be an oxazolyl group, but is not limited thereto.

In one embodiment, the aforementioned R _b and R _c may be the same or different functional groups.

In one embodiment, the aforementioned R _b and R _c are independently selected from the group consisting of Wherein X may be hydrogen, halogen, cyano, trifluoromethyl, amine or C ₁ -C ₁₀ alkyl, but is not limited thereto.

The present invention further provides an organic light emitting diode device comprising: a pair of electrodes; and an organic light emitting unit disposed between the pair of electrodes, wherein the organic light emitting unit comprises a compound having the structure represented by the above formula (I) :

The present invention further provides an organic electroluminescent device comprising: a pair of electrodes; and an organic light emitting unit disposed between the pair of electrodes, wherein the organic light emitting unit comprises a light emitting layer, the light emitting layer comprising a host material and a doping material, and the host material comprises a compound having the structure of the above formula (I): In one embodiment, the organic light emitting diode device described above, wherein the dopant material may comprise 0-10% of a green light doping material. In a specific implementation, the green light doping material may be Ir(ppy) ₃ , but is not limited thereto.

In one embodiment, the foregoing organic light emitting diode device, wherein the dopant material may comprise 0 to 10% of an orange light doping material. In a specific implementation, the orange light doping material may be Ir(pq) ₃ , but is not limited thereto.

In one embodiment, the organic light emitting diode device described above, wherein the dopant material comprises 0 to 10% of a red light doping material. In a specific embodiment, the red light doping material is Ir(piq) ₃ , but is not limited thereto.

Next, the embodiment of the present invention is described in detail by the following examples, but is not limited thereto. The above and other objects, features and advantages of the present invention will become more apparent from

壹, compound synthesis

Referring to the following formula, the quinoline and carbazole-containing compounds of the examples of the present invention are prepared by the following scheme.

1-(4-(9H-carbazol-9-yl)phenyl)ethanone and 2-aminobenzophenone (2) -aminobenzophenone) is a starting material, diphenyl phosphate (DPP), and m -cresol ( m -cresol) at 140 degrees to give a CzPPQ derivative. The preparation of other compounds containing quinoline and carbazole can also be obtained by adjusting the starting materials.

Preparation Example 1: Preparation of CzPPQ [9-(4-(4-phenylquinolin-2-yl)phenyl)-9H-carbazole (9-(4-(4-phenylquinolin-2-yl)phenyl)- 9H-carbazole)

1-(4-(9H-carbazol-9-yl)phenyl)ethanone (285 mg, 1.00 mmol) starting from 1-(4-(9H-carbazol-9-yl)phenyl)ethanone) 2-aminobenzophenone (400 mg, 2.00 mmol), diphenyl phosphate (DPP, 751 mg, 3.00 mmol) and freshly distilled m -cresol ( m - Cresol) (1.0 mL) was added to a round bottom flask and heated to 140 °C for 12 hours under nitrogen. After completion of the reaction, the precipitate was filtered after adding 10% triethylamine/methanol, and subjected to column chromatography at a ratio of hexane/ethyl acetate = 10:1 to obtain the product 9-(4-(4-phenylquinoline- 2-(4-(4-phenylquinolin-2-yl)phenyl)-9H-carbazole) 381 mg, yield 85.4%.

The analytical data for this product are as follows: ¹ H NMR (400 MHz, CDCl ₃ , δ): 7.31 (dd, 2H, J = 7.6, 7.2 Hz), 7.44 (dd, 2H, J = 8.0, 7.6 Hz), 7.50- 7.62 (m, 8H), 7.73-7.80 (m, 3H), 7.91 (s, 1H), 7.95 (d, 1H, J = 8.4 Hz), 8.16 (d, 2H, J = 7.6 Hz), 8.30 (d) , 1H, J = 8.4 Hz), 8.43 (d, 2H, J = 8.4 Hz); ¹³ C NMR (100 MHz, CDCl ₃ , δ): 109.8, 119.1, 120.1, 120.3, 123.5, 125.7, 125.8, 126.0, 126.5, 127.2, 128.5, 128.6, 129.0, 129.5, 129.7, 130.1, 138.2, 138.5, 138.7, 140.6, 148.8, 149.4, 155.9; HRMS (EI, m/z): [ M ⁺ ]calcd for C ₃₃ H ₂₂ N _{2, 446.1783; found, 446.1779.Anal.calcd.for C} 33 H 22 N 2: C 88.76, H 4.97, N 6.27; found: C 88.49, H 4.87, N 6.35.

Preparation Example 2: Preparation of CzPPBrQ [9-(4-(4-(4-bromophenyl)quinolin-2-yl)phenyl)-9H-carbazole (9-(4-(4-(4-bromophenyl)) )quinolin-2-yl)phenyl)-9H-carbazole)]

1-(4-(9H-carbazol-9-yl)phenyl)ethanone (285 mg, 1.00 mmol) starting from 1-(4-(9H-carbazol-9-yl)phenyl)ethanone) , (2-aminophenyl)(4-bromophenyl)methanone (553 mg, 2.00 mmol), diphenyl phosphate (DPP, 751 mg, 3.00 Methyl) and freshly distilled m -cresol (1.0 mL) were added to a round bottom flask and heated to 140 °C for 12 hours under nitrogen. After completion of the reaction, the precipitate was filtered after adding 10% triethylamine/methyl, and subjected to column chromatography at a ratio of hexane/ethyl acetate = 10:1 to obtain the product 9-(4-(4-(4-bromobenzene). 9-(4-(4-(4-bromophenyl)quinolin-2-yl)phenyl)-9H-carbazole) 426 mg, yield 81.2 %.

The analytical data for this product are as follows: ¹ H NMR (400 MHz, CDCl ₃ , δ): 7.30 (dd, 2H, J = 7.2, 7.2 Hz), 7.40-7.52 (m, 7H), 7.69-7.80 (m, 7H) ), 7.86-7.88 (m, 2H), 8.14 (d, 2H, J = 7.2 Hz), 8.27 (d, 1H, J = 8.8 Hz), 8.41 (d, 2H, J = 8.4 Hz),; ¹³ C NMR (100 MHz, CDCl ₃ , δ): 109.8, 119.0, 120.1, 120.4, 122.9, 123.6, 125.3, 125.5, 126.0, 126.8, 127.3, 129.1, 129.9, 130.3, 131.2, 131.9, 137.2, 138.4, 138.9, 140.7 , 148.2, 148.9, 156.0; HRMS (EI, m/z): [ M ⁺ ]calcd for C ₃₃ H ₂₁ BrN ₂ , 524.0888; found, 524.0893.

Preparation 3: Preparation of CzPPQBr [9-(4-(6-bromo-4-phenylquinolin-2-yl)phenyl)-9H-carbazole (9-(4-(6-bromo-4-phenylquinolin) -2-yl)phenyl)-9H-carbazole)

1-(4-(9H-carbazol-9-yl)phenyl)ethanone (285 mg, 1.00 mmol) starting from 1-(4-(9H-carbazol-9-yl)phenyl)ethanone) , (2-amino-5-bromophenyl)(phenyl)methanone (553 mg, 2.00 mmol), diphenyl phosphate (DPP, 751 Mg, 3.00 mmol) and freshly distilled m -cresol (1.0 mL) were added to a round bottom flask and heated to 140 °C for 12 hours under nitrogen. After completion of the reaction, the precipitate was filtered after adding 10% triethylamine/methanol, and subjected to column chromatography at a ratio of hexane/ethyl acetate = 10:1 to give the product 9-(4-(6-bromo-4-benzene). 9-(4-(6-bromo-4-phenylquinolin-2-yl)phenyl)-9H-carbazole) 437 mg, yield 83.2% .

The analytical data for this product are as follows: ¹ H NMR (400 MHz, CDCl ₃ , δ): 7.30 (ddd, 2H, J = 8.0, 7.6, 1.0 Hz), 7.42 (ddd, 2H, J = 8.0, 6.8, 1.2 Hz ), 7.48-7.50 (m, 2H), 7.55-7.60 (m, 5H), 7.73 (d, 2H, J = 8.4 Hz), 7.82 (dd, 1H, J = 9.0, 6.2 Hz), 7.91 (s, 1H), 8.07 (d, 1H, J = 3.0 Hz ), 8.13-8.16 (m, 3H), 8.41 (d, 2H, J = 8.4 Hz); ¹³ C NMR (100 MHz, CDCl ₃ , δ): 109.7 , 109.8, 119.9, 120.2, 120.4, 120.7, 123.6, 126.4, 127.1, 127.3, 127.9, 128.8, 128.9, 129.1, 129.4, 131.8, 133.3, 137.6, 138.0, 139.1, 140.6, 148.8, 156.2; HRMS (EI, m /z): [ M ⁺ ]calcd for C ₃₃ H ₂₁ BrN ₂ , 524.0888; found, 524.0897.

Preparation Example 4: Preparation of CzPPCzQ [9,9'-(quinoline-2,4-diylbis(4,1-phenylene)) bis(9H-carbazole) (9,9'-(quinoline-2) ,4-diylbis(4,1-phenylene))bis(9H-carbazole))

The starting material is 9-(4-(4-(4-bromophenyl)quinolin-2-yl)phenyl)-9H-carbazole (9-(4-(4-(4-bromophenyl)quinolin-) 2-yl)phenyl)-9H-carbazole) (525 mg, 1.00 mmol), carbazole (200 mg, 1.2 mmol), Pd(dba) ₂ (33 mg, 0.060 mmol), tri-tert-butylphosphine (tri) - tert -butylphosphine) (96 mg, 0.048 mmol), sodium tert-(sodium tert -butoxide) (432 mg , 4.50 mmol) and a solvent o-xylene (o -xylene) (3.00 mL) was added to the high pressure tube butanol, After heating to 150 degrees, the reaction was carried out for 48 hours. After the completion of the reaction, the metal salt was removed by Celite and washed repeatedly with dichloromethane for several times, after which the filtrate was collected and concentrated, and finally subjected to column chromatography to obtain a product in a ratio of hexane/ethyl acetate = 10:1. 9,9'-(quinoline-2,4-diylbis(4,1-phenylene)) bis(9H-carbazole (9,9'-(quinoline-2,4-diylbis(4,1) -phenylene))bis(9H-carbazole)) 528 mg, yield 86.3%.

The analytical data for this product are as follows: ¹ H NMR (400 MHz, CDCl ₃ , δ): 7.28-7.33 (m, 4H), 7.39-7.46 (m, 7H), 7.51 (dd, 4H, J = 8.0, 8.0 Hz ), 7.61 (d, 2H, J = 7.2 Hz), 7.78 (d, 2H, J = 8.4 Hz), 7.96 (d, 1H, J = 8.8 Hz), 8.00 (s, 1H), 8.11-8.18 (m) , 5H), 8.47-8.51 (m, 3H); ¹³ C NMR (100 MHz, CDCl ₃ , δ): 109.5, 109.8, 120.0, 120.2, 120.3, 120.3, 120.4, 123.1, 123.5, 123.6, 126.0, 126.1, 126.6, 127.2, 128.9, 129.2, 129.3, 131.7, 135.8, 137.5, 139.2, 140.6, 140.7, 156.2; HRMS (EI, m/z): [ M ⁺ ]calcd for C ₄₅ H ₂₉ N ₃ , 611.2361; 611.2365.Anal.calcd.for C ₄₅ H ₂₉ N ₃ :C 88.35,H 4.78,N 6.87;found:C 88.15,H 4.74,N 7.02.

Preparation 5: Preparation of CzPPQCz [9-(4-(6-(9H-carbazol-9-yl)-4-phenylquinolin-2-yl)phenyl)-9H-carbazole (9-(4) -(6-(9H-carbazol-9-yl)-4-phenylquinolin-2-yl)phenyl)-9H-carbazole)]

Starting material 9-(4-(6-bromo-4-phenylquinolin-2-yl)phenyl)-9H-carbazole (9-(4-(6-bromo-4-phenylquinolin-2-) Yl)phenyl)-9H-carbazole) (525 mg, 1.00 mmol), carbazole (200 mg, 1.2 mmol), Pd(dba) ₂ (33 mg, 0.060 mmol), tri-tert-butylphosphine ( tri- tert -butylphosphine) (96 mg, 0.048 mmol), sodium tert-butoxide (sodium tert -butoxide) (432 mg , 4.50 mmol) and a solvent o-xylene (o -xylene) (3.00 mL) was added to a high pressure tube After heating to 150 degrees, the reaction was carried out for 48 hours. After completion of the reaction, the metal salt was removed by Celite and washed repeatedly with dichloromethane for several times, after which the filtrate was collected and concentrated, and finally subjected to column chromatography at a ratio of hexane/EtOAc = 10:1 to obtain the product 9-( 4-(6-(9H-carbazol-9-yl)-4-phenylquinolin-2-yl)phenyl)-9H-carbazole (9-(4-(6-(9H-carbazol-9) -yl)-4-phenylquinolin-2-yl)phenyl)-9H-carbazole)) 524 mg, yield 85.7%.

The analytical data of this product are as follows: ¹ H NMR (400 MHz, CDCl ₃ , δ): 7.30-7.37 (m, 4H), 7.43-7.54 (m, 6H), 7.58-7.64 (m, 3H), 776-7.87 (m, 7H), 8.03 (s, 1H), 8.10 (d, 1H, J = 8.4 Hz), 8.16-8.21 (m, 4H), 8.35 (d, 2H, J = 8.8 Hz), 8.48 (d, 2H, J = 8.4 Hz); ¹³ C NMR (100 MHz, CDCl ₃ , δ): 109.7, 109.8, 119.3, 120.1, 120.3, 120.4, 120.5, 123.5, 123.6, 125.5, 125.7, 126.0, 126.1, 126.8, 127.1 , 127.3, 129.1, 139.9, 130.0, 131.1, 137.2, 138.1, 138.5, 138.9, 14.07, 148.5, 149.0, 156.0; HRMS (EI, m/z): [ M ⁺ ]calcd for C ₄₅ H ₂₉ N ₃ , 611.2361 ;found,611.2367.Anal.calcd.for C ₄₅ H ₂₉ N ₃ :C 88.35,H 4.78,N 6.87;found:C 88.25,H 4.96,N 6.54.

Preparation 6: Preparation of CzPPtBuPhQ [9-(-4-(4-(4'-(tert-butyl)-[1,1'-biphenyl]-4-yl)quinolin-2-yl)phenyl) -9H-carbazole (9-(4-(4-(4'-(tert-butyl)-[1,1'-biphenyl]-4-yl)quinolin-2-yl)phenyl)-9H-carbazole) 】

1-(4-(9H-carbazol-9-yl)phenyl)ethanone (285 mg, 1.00 mmol), 4- Tert-butylphenylboronic acid (0.36g, 2.00mmole) and potassium carbonate (3.32g, 24.00mmole) were placed in a single-necked flask, and water (12ml) and toluene (36ml) were added simultaneously to the temperature of 60 ° C. Nitrogen was added several times with rapid addition of Pd(PPh ₃ ) ₄ (0.06 g, 0.05 mmole) and finally nitrogen was pumped several times and reacted at 100 ° C for one day. After the reaction was completed, it was extracted with ethyl acetate and water, and the organic layer was evaporated, evaporated, and evaporated. Finally, column chromatography was carried out at a ratio of hexane/ethyl acetate = 10:1 to give the product 9-(-4-(4-(4'-(tert-butyl)-[1,1'-biphenyl]- 4-yl)quinolin-2-yl)phenyl)-9H-carbazole 9-(4-(4-(4'-(tert-butyl)-[1,1'-biphenyl]-4-yl) Quinolin-2-yl)phenyl)-9H-carbazole 501 mg, yield 86.7%.

The analytical data for this product are as follows: ¹ H NMR (400 MHz, CDCl ₃ , δ ): 1.40 (s, 9H), 7.30 (dd, 2H, J = 7.2, 7.6 Hz), 7.41 to 7.44 (m, 2H), 7.49-7.56 (m, 5H), 7.64-7.68 (m, 3H), 7.73-7.80 (m, 5H), 7.95 (s, 1H), 8.03 (d, 1H, J = 8.4 Hz), 8.15 (d, 1H, J = 7.6 Hz), 8.29 (d, 1H, J = 8.4 Hz), 8.43 (d, 1H, J = 8.4 Hz), ¹³ C NMR (100 MHz, CDCl ₃ , δ ): 31.4, 34.6, 109.8, 119.2, 1201, 120.3, 123.5, 125.8, 125.9, 126.0, 126.1, 126.6, 126.8, 127.2, 127.3, 129.1, 129.8, 130.0, 130.2, 136.9, 137.5, 138.7, 138.8, 140.7, 141.3, 148.9, 149.2, 150.8, 156.0; HRMS (EI, m/z): [ M ⁺ ]calcd for C ₃₃ H ₂₁ BrN ₂ , 578.2722; found, 578.2714.

Preparation Example 7: Preparation of CzPPQtBuPh [9-(4-(6-(4-(tert-butyl)phenyl)-4-phenylquinolin-2-yl)phenyl)-9H-carbazole 9-(4) -(6-(4-(tert-butyl)phenyl)-4-phenylquinolin-2-yl)phenyl)-9H-carbazole]

1-(4-(9H-carbazol-9-yl)phenyl)ethanone (285 mg, 1.00 mmol), 4- Tert-butylphenylboronic acid (0.36g, 2.00mmole) and potassium carbonate (3.32g, 24.00mmole) were placed in a single-necked flask, and water (12ml) and toluene (36ml) were added simultaneously to the temperature of 60 ° C. Nitrogen was added several times with rapid addition of Pd(PPh ₃ ) ₄ (0.06 g, 0.05 mmole) and finally nitrogen was pumped several times and reacted at 100 ° C for one day. After completion of the reaction, the mixture was extracted with ethyl acetate and water. Finally, column chromatography was carried out at a ratio of hexane/ethyl acetate=10:1 to give the product 9-(4-(6-(4-(tert-butyl)phenyl)-4-phenylquinolin-2-yl)phenyl) -9H-carbazole 497 mg, yield 88.6%.

The analytical data for this product are as follows: ¹ H NMR (400 MHz, CDCl ₃ , δ ): 1.35 (s, 9H), 7.30 (dd, 2H, J = 7.6, 7.2 Hz), 7.40-7.65 (m, 13H), 7.43 (d, 2H, J = 7.6), 7.91 (s, 1H), 8.02 (d, 1H, J = 8.8 Hz), 8.11 (s, 1H), 8.15 (d, 2H, J = 7.6 Hz), 8.31 (d, 2H, J = 8.4 Hz), 8.43 (d, 1H, J = 7.6 Hz); ¹³ C NMR (100 MHz, CDCl ₃ , δ ): 31.3, 34.6, 109.9, 119.6, 1201, 1203, 123.2, 123.5, 125.8, 126.0, 126.1, 127.1, 127.3, 128.6, 128.7, 128.9, 129.4, 129.6, 130.5, 137.7, 138.4, 138.7, 139.2, 140.7, 148.2, 149.6, 150.8, 155.7; HRMS (EI, m/z) :[ M ⁺ ]calcd for C ₃₃ H ₂₁ BrN ₂ ,578.2722;found,578.2730.

Energy level and thermal stability of hydrazine, quinoline and carbazole-containing compounds

For the results of the energy level and thermal stability of the quinoline and carbazole-containing compounds of the above preparations and the conventionally used host material CBP, please refer to Table 1, wherein CzPPCzQ and CzPPQCz have better glass transition temperature and decomposition. temperature.

Reference, organic light emitting diode structure

Referring to the first drawing, which is a schematic view showing the structure of an organic electroluminescent device comprising a bipolar compound containing quinoline and carbazole according to the present invention, the organic electroluminescent device 10 comprises a substrate 12, The electrode 14, the organic light emitting unit 16, and an upper electrode 18 are next. The organic electroluminescent device 10 is provided. The organic light-emitting unit 16 includes a light-emitting layer, and the light-emitting layer material comprises the bipolar compound containing quinoline and carbazole. The bipolar compound containing quinoline and carbazole may be a host luminescent material or a dopant of the luminescent layer. In this embodiment, the compound containing quinoline and carbazole is a luminescent layer. One of the main body luminescent materials.

In addition, in this embodiment, the organic electroluminescent device 10 optionally includes: a hole blocking layer, an exciton blocking layer, an electron blocking layer, and an electron injecting layer, that is, whether it is suitable for those skilled in the art to determine whether or not These layered structures are employed.

Hereinafter, the compounds containing quinoline and carbazole were respectively applied to green, orange, and red organic light-emitting diodes, and their effects were tested.

Test Example 1. Green Organic Light Emitting Diode

The individual detailed structure of the exemplified green organic light-emitting diode test device and its thickness (in nm) are as follows: G: NPB (20) / TCTA (10) / 7% Ir (ppy) ₃ : CzPPQ analog (30) )/BCP(10)/Alq(40)/LiF(1)

The formed doped organic light emitting diode structure. Among them, ITO (indium tin oxide) was used as the substrate, and the electrode materials tested included LiF/Al, and the tested hole transport layer TCTA (4,4',4"-N-tris(carbazole-9-) Triphenylamine, 4,4,4-tri(N-carbazolyl)triphenylamine, NPB (N,N'-Bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine); Electron transport layer BAlq. The compound containing quinoline and carbazole in this embodiment is used as the main light-emitting material of the light-emitting layer, and the host material CBP (4,4'-bis(9H-carbazol-9-yl)biphenyl) 4,4'-Bis(9H-carbazol-9-yl)biphenyl) was used as a control group, and dopants were added to the light-emitting layers of different organic light-emitting materials, wherein the green organic light-emitting diodes were doped 7% Ir(ppy) ₃ (tris(2-phenylpyridine)iridium(III)), the potency is listed in Table 2: Table 2. Green-light organic light-emitting diodes with compounds containing quinoline and carbazole

Test Example 2. Orange Organic Light Emitting Diode

The individual detailed structure of the exemplified orange organic light-emitting diode test device and its thickness (in nm) are as follows: O: NPB (20) / TCTA (10) / 4% Ir (pq) ₃ : CzPPQ analog ( 30) / BCP (15) / Alq (50) / LiF (1)

The formed doped organic light-emitting diode structural element is the same as the above, and will not be described herein. Among them, the orange organic light-emitting diode is doped with 4% Ir(pq) ₃ (tris(2-phenylquinoline) iridium(III)), and the performance is listed in Table 3: Note: V _d : drive voltage; η _ext : external quantum efficiency; L : maximum brightness; η _c : current efficiency; η _p : electrical energy efficiency; λ _em : emission wavelength

Test Example 3. Orange Organic Light Emitting Diode

The individual detailed architecture of the illustrated red organic light-emitting diode test device and its thickness (in nm) are as follows: R: NPB (20) / TCTA (10) / 7% Ir (piq) ₃ : CzPPQ analog (30) )/BCP(15)/Alq(50)/LiF(1)

The formed doped organic light-emitting diode structural element is the same as above, wherein the red organic light-emitting diode is doped with 7% Ir(piq) ₃ (tris(1-phenylisoquinolinolato)iridium(III)), The performance is listed in Table 4:

Test Example 4. Green organic light-emitting diode (added to hole injection material NPNPB)

The individual detailed structure of the exemplified green organic light-emitting diode test device and its thickness (in nm) are as follows: G: NNPBP (60) / NPB (10) / TCTA (10) / 7% Ir (ppy) ₃ : CzPPQ analog (30) / BAlq (30) / LiF (1)

The illustrated green organic light-emitting diode test device is further filled with a hole injection material NPNBP, and the results are shown in Table 5-1 and Table 5-2.

Test Example 6. Orange Organic Light Emitting Diode (Adding Hole Injection Material NPNPB)

The individual detailed structure of the exemplified orange organic light-emitting diode test device and its thickness (in nm) are as follows: O: NNPBP (60) / NPB (10) / TCTA (10) / 4% Ir (pq) ₃ :CzPPQ similarity (30)/BAlq(30)/LiF(1)

The results of the illustrated orange organic light-emitting diode test device are shown in Table 6-1 and Table 6-2.

Test Example 7. Red Organic Light Emitting Diode (Adding Hole Injecting Material NPNPB)

The individual detailed architecture of the illustrated red organic light-emitting diode test device and its thickness (in nm) are as follows: R: NNPBP (60) / NPB (10) / TCTA (10) / 4% Ir (piq) ₃ : CzPPQ analog (30) / BAlq (30) / LiF (1)

The results of the exemplified red organic light emitting diode test device are shown in Table 7-1 and Table VII-2.

Note: η _ext : external quantum efficiency; η _c : current efficiency; η _p : electrical energy efficiency

Component life test of an organic light-emitting diode device having a compound containing quinoline and carbazole

The luminescence efficiency of the organic light-emitting diode was measured by the devices A, E, H, and I, and the life of the device was tested. The components of the device are listed below: Device A: ITO/NPB (20 nm) / TCTA (10 nm) / CzPPQ: Ir (piq) ₃ (4 wt%) (30 nm) / BCP (15 nm) / Alq ₃ (50 nm) / LiF (1 nm) / Al (100 nm)

Apparatus E: ITO/NPB (20 nm) / TCTA (10 nm) / CBP: Ir(piq) ₃ (4 wt%) (30 nm) / BCP (15 nm) / Alq ₃ (50 nm) / LiF (1 nm) / Al (100nm)

Apparatus H: ITO/NPB (20 nm) / TCTA (10 nm) / CBP: Ir(pq) ₃ (4 wt%) (30 nm) / BCP (15 nm) / Alq ₃ (50 nm) / LiF (1 nm) / Al (100nm)

Apparatus I: ITO/NPB (20 nm) / TCTA (10 nm) / CzPPQ: Ir(pq) ₃ (4 wt%) (30 nm) / BCP (15 nm) / Alq ₃ (50 nm) / LiF (1 nm) / Al (100nm)

Please refer to the second figure, which is a line graph showing the data of the attenuation efficiency of the devices A, E, H, and I with time, wherein the devices A and I using CzPPQ as the luminescent material are compared with the control group E using CBP. And the luminous efficiency of H is significantly slower.

In addition, the component lifetime test was carried out under conditions of 500 cd m ^-2 and brightness reduction of 40% (T60). As shown in Table 8, it was found that CzPPQ was used as the luminescent material among the red and orange organic light-emitting diodes. The device lifetimes of devices A and I are 8991 and 19111, respectively, and the component life is much higher than that of the control groups E and H using CBP.

In summary, the bipolar compound containing quinoline and carbazole of the present invention does greatly improve the hole transport efficiency. When the bipolar compound provided by the present technology is used as the host material of the light-emitting layer of the organic light-emitting diode, the luminous efficiency and electrical properties of the OLED can be improved. And it can exhibit excellent luminous efficiency and long component life. Therefore, the bipolar compound of the present invention has the potential to replace the existing host material, and is used to produce an OLED device having excellent luminous efficiency.

It will be apparent to those skilled in the art that various changes can be made in accordance with the embodiments of the present invention without departing from the spirit of the invention. Therefore, it is to be understood that the invention is not limited by the scope of the invention, and is intended to cover the modifications of the spirit and scope of the invention.

10‧‧‧Organic electroluminescent device

12‧‧‧Base

14‧‧‧ lower electrode

16‧‧‧Organic lighting unit

18‧‧‧Upper electrode

The first figure is a schematic view showing the structure of an organic light-emitting diode obtained by using a compound containing quinoline and carbazole in an embodiment of the present invention.

The second graph is the line graph data in which the luminous efficiency of the devices A, E, H, and I is weakened with time.

10‧‧‧Organic electroluminescent device

12‧‧‧Base

14‧‧‧ lower electrode

16‧‧‧Organic lighting unit

18‧‧‧Upper electrode

Claims (14)

A bipolar compound containing quinoline and carbazole having the structure shown in the following formula (I): Wherein A is phenyl, biphenyl or triphenyl; R _a , R _b , R _c are independently selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, amine, C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, C ₂ -C ₁₀ alkynyl, C ₃ -C ₂₀ cycloalkyl, C ₃ -C ₂₀ cycloalkenyl, C ₁ -C ₂₀ heterocycloalkyl, C ₁ -C ₂₀ heterocycloalkenyl a group consisting of a aryl group, an aryl group, and a heteroaryl group. The bipolar compound according to claim 1, wherein the A system further has a substituent consisting of hydrogen, halogen, cyano, trifluoromethyl, amine, C ₁ -C ₁₀ alkane. , C ₂ -C ₁₀ alkenyl, C ₂ -C ₁₀ alkynyl, C ₃ -C ₂₀ cycloalkyl, C ₃ -C ₂₀ cycloalkenyl, C ₁ -C ₂₀ heterocycloalkyl, C ₁ -C ₂₀ heterocycloalkenyl, aryl and heteroaryl. The bipolar compound according to claim 1 or 2, wherein the aryl group is a phenyl group or a substituted phenyl group. The bipolar compound according to claim 1 or 2, wherein the heteroaryl group is a carbazolyl group. The bipolar compound of claim 1, wherein R _b and R _c are different. The bipolar compound according to claim 1, wherein R _b and R _c are independently selected from the group consisting of Wherein X is hydrogen, halogen, cyano, trifluoromethyl, amine or C ₁ -C ₁₀ alkyl. An organic light emitting diode device comprising: a pair of electrodes; and an organic light emitting unit disposed between the pair of electrodes, wherein the organic light emitting unit comprises a compound having the structure of the formula (I): Wherein A is phenyl, biphenyl or triphenyl; R _a , R _b , R _c are independently selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, amine, C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, C ₂ -C ₁₀ alkynyl, C ₃ -C ₂₀ cycloalkyl, C ₃ -C ₂₀ cycloalkenyl, C ₁ -C ₂₀ heterocycloalkyl, C ₁ -C ₂₀ heterocycloalkenyl a group consisting of a aryl group, an aryl group, and a heteroaryl group. An organic electroluminescent device includes: a pair of electrodes; and an organic light emitting unit disposed between the pair of electrodes, wherein the organic light emitting unit comprises a light emitting layer, the light emitting layer comprising a host material and a doping material And the host material comprises a compound having the structure of formula (I): Wherein A is phenyl, biphenyl or triphenyl; R _a , R _b , R _c are independently selected from the group consisting of hydrogen, halogen, cyano, trifluoromethyl, amine, C ₁ -C ₁₀ alkyl, C ₂ -C ₁₀ alkenyl, C ₂ -C ₁₀ alkynyl, C ₃ -C ₂₀ cycloalkyl, C ₃ -C ₂₀ cycloalkenyl, C ₁ -C ₂₀ heterocycloalkyl, C ₁ -C ₂₀ heterocycloalkenyl a group consisting of a aryl group, an aryl group, and a heteroaryl group. The organic light emitting diode device of claim 8, wherein the doping material comprises 0 to 10% of a green light doping material. The organic light-emitting diode device according to claim 9, wherein the green light-doping material is Ir(ppy) ₃ . The organic light emitting diode device of claim 8, wherein the doping material comprises 0 to 10% of an orange light doping material. The organic light-emitting diode device according to claim 11, wherein the orange light-doping material is Ir(pq) ₃ . The organic light emitting diode device of claim 8, wherein the doping material comprises 0 to 10% of a red light doping material. The organic light emitting diode device of claim 13, wherein the red light doping material is Ir(piq) ₃ .